1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22337637, compound

HRID 586087Notes

Reaction equation

HRID 586087 reaction equation
ClC(Cl)(Cl)[C:3]([NH:5][C:6]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]2[C:7]=1[CH:8]=[N:9][NH:10]2)=[O:4].[C:18]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].N12CCCN=C1CCCCC2>CC#N>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([CH2:26][NH:27][C:3]([NH:5][C:6]2[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]3[C:7]=2[CH:8]=[N:9][NH:10]3)=[O:4])=[CH:28][CH:29]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27356554-tert-ButylbenzylamineHCID 22337658HCID 22337658, compound

Product 1

HCID 22337637HCID 22337637, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,2,2-Trichloro-N-(7-methyl-1H-indazol-4-yl)acetamide (72 mg, 0.25 mmol), 4-tert-butylbenzylamine (55 mg, 0.34 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.09 mL, 0.60 mmol) were combined in CH3CN (6 mL) and refluxed overnight. The mixture was allowed to cool to ambient temperature and was concentrated under reduced pressure. The residue was taken up in ethyl acetate and washed twice with saturated aqueous NH4Cl solution. The organic layer was dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with ethyl acetate to provide the title compound. The corresponding hydrochloride salt was prepared with methanolic HCl. 1H NMR (300 MHz, d6-DMSO) δ 12.90 (br s, 1H), 7.94 (d, J=1.3 Hz, 1H), 7.91 (s, 1H), 7.47 (m, 2H), 7.37 (m, 2H), 7.25 (m, 2H), 6.84 (t, J=5.8 Hz, 1H), 4.26 (d, J=5.7 Hz, 2H), 2.35 (s, 3H), 1.27 (s, 9H); MS (ESI+) m/z 337 (M+H)+.

Workup

  1. temperaturerefluxed overnight
  2. concentrationwas concentrated under reduced pressure
  3. washwashed twice with saturated aqueous NH4Cl solution
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-3820c8f438b54657b9a5299f3ee33744
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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